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| index2_label = as salt | index2_label = Sodium
| CAS_number2_Ref = {{cascite|correct|CAS}} | CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 52123-49-6 | CAS_number2 = 52123-49-6

Revision as of 16:20, 2 September 2022

Cephalosporin antibiotic Pharmaceutical compound
Cefazaflur
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (6R,7R)-3--8-oxo-7-(amino)-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H13F3N6O4S3
Molar mass470.46 g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS12NC(=O)CSC(F)(F)F)CSc3nnnn3C)C(=O)O
InChI
  • InChI=1S/C13H13F3N6O4S3/c1-21-12(18-19-20-21)28-3-5-2-27-10-7(9(24)22(10)8(5)11(25)26)17-6(23)4-29-13(14,15)16/h7,10H,2-4H2,1H3,(H,17,23)(H,25,26)/t7-,10-/m1/s1
  • Key:HGXLJRWXCXSEJO-GMSGAONNSA-N
  (verify)

Cefazaflur (INN) is a first-generation cephalosporin antibiotic.

Synthesis

Cefazaflur stands out among this group of analogues because it lacks an arylamide C-7 side chain (see cephacetrile for another example).

Cefazaflur synthesis:

Cefazaflur is synthesized by reaction of 3-(1-methyl-1H-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid (1) with trifluoromethylthioacetyl chloride (2).

References

  1. DeMarinis RM, Boehm JC, Dunn GL, Hoover JR, Uri JV, Guarini JR, et al. (January 1977). "Semisynthetic cephalosporins. Synthesis and structure-activity relationships of analogues with 7-acyl groups derived from 2-(cyanomethylthio)acetic acid or 2-acetic acid and their sulfoxides and sulfones". Journal of Medicinal Chemistry. 20 (1): 30–5. doi:10.1021/jm00211a006. PMID 319233.
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Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
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β-lactamase sensitive
(1st generation)
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Extended
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Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
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Cephems
Cephalosporins
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  • Inhibits PG elongation and crosslinking: Ramoplanin
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